# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Chang-Chuan Chou' _publ_contact_author_email ccchou@mail.cgit.edu.tw loop_ _publ_author_name 'Chang-Chuan Chou' 'Hsueh-Ju Liu' data_8903 _database_code_depnum_ccdc_archive 'CCDC 722446' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H30 N6' _chemical_formula_sum 'C29 H30 N6' _chemical_formula_weight 462.59 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.7905(2) _cell_length_b 19.1349(4) _cell_length_c 13.3567(3) _cell_angle_alpha 90.00 _cell_angle_beta 113.4740(10) _cell_angle_gamma 90.00 _cell_volume 2529.59(9) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 16827 _cell_measurement_theta_min 2.037 _cell_measurement_theta_max 25.028 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.215 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8775 _exptl_absorpt_correction_T_max 1.0739 _exptl_absorpt_process_details ; ? ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23998 _diffrn_reflns_av_R_equivalents 0.0740 _diffrn_reflns_av_sigmaI/netI 0.0584 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 25.02 _reflns_number_total 4448 _reflns_number_gt 2915 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1993P)^2^+4.5856P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment fixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.044(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4448 _refine_ls_number_parameters 317 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1165 _refine_ls_R_factor_gt 0.0727 _refine_ls_wR_factor_ref 0.2530 _refine_ls_wR_factor_gt 0.1932 _refine_ls_goodness_of_fit_ref 0.765 _refine_ls_restrained_S_all 0.765 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N -0.1794(3) 0.00170(15) 0.0048(2) 0.0390(7) Uani 1 1 d . . . N2 N -0.2108(3) 0.06769(14) -0.0369(2) 0.0352(7) Uani 1 1 d . . . N3 N -0.0863(3) 0.16005(14) 0.0841(2) 0.0344(7) Uani 1 1 d . . . N4 N 0.1058(3) 0.09579(14) 0.2075(2) 0.0321(7) Uani 1 1 d . . . N5 N 0.2868(3) 0.01637(15) 0.4238(2) 0.0369(7) Uani 1 1 d . . . N6 N 0.1661(3) 0.00106(14) 0.3402(2) 0.0338(7) Uani 1 1 d . . . C1 C -0.3066(5) -0.1044(2) 0.0078(4) 0.0560(11) Uani 1 1 d . . . H1A H -0.2152 -0.1219 0.0503 0.084 Uiso 1 1 calc R . . H1B H -0.3491 -0.1329 -0.0581 0.084 Uiso 1 1 calc R . . H1C H -0.3604 -0.1072 0.0520 0.084 Uiso 1 1 calc R . . C2 C -0.2993(4) -0.02970(19) -0.0240(3) 0.0407(9) Uani 1 1 d . . . C3 C -0.4039(4) 0.0149(2) -0.0837(3) 0.0442(9) Uani 1 1 d . . . H3 H -0.4975 0.0040 -0.1142 0.053 Uiso 1 1 calc R . . C4 C -0.3464(4) 0.07759(19) -0.0902(3) 0.0377(8) Uani 1 1 d . . . C5 C -0.4056(4) 0.1455(2) -0.1427(3) 0.0516(10) Uani 1 1 d . . . H5A H -0.3331 0.1796 -0.1295 0.077 Uiso 1 1 calc R . . H5B H -0.4682 0.1628 -0.1117 0.077 Uiso 1 1 calc R . . H5C H -0.4545 0.1386 -0.2215 0.077 Uiso 1 1 calc R . . C6 C -0.1039(3) 0.11882(17) -0.0143(3) 0.0347(8) Uani 1 1 d . . . H6A H -0.1262 0.1506 -0.0776 0.042 Uiso 1 1 calc R . . H6B H -0.0183 0.0947 -0.0031 0.042 Uiso 1 1 calc R . . C7 C 0.0006(3) 0.21942(17) 0.0945(3) 0.0333(8) Uani 1 1 d . . . C8 C -0.0511(4) 0.28038(19) 0.0403(3) 0.0441(9) Uani 1 1 d . . . H8 H -0.1454 0.2846 -0.0016 0.053 Uiso 1 1 calc R . . C9 C 0.0357(4) 0.33681(19) 0.0468(3) 0.0496(10) Uani 1 1 d . . . H9 H -0.0008 0.3792 0.0099 0.059 Uiso 1 1 calc R . . C10 C 0.1710(4) 0.33118(19) 0.1055(3) 0.0468(10) Uani 1 1 d . . . H10 H 0.2279 0.3697 0.1084 0.056 Uiso 1 1 calc R . . C11 C 0.2288(4) 0.26905(19) 0.1622(3) 0.0404(9) Uani 1 1 d . . . C12 C 0.1415(3) 0.21273(17) 0.1575(3) 0.0329(8) Uani 1 1 d . . . C13 C 0.1975(3) 0.14846(18) 0.2131(3) 0.0329(8) Uani 1 1 d . . . C14 C 0.3345(4) 0.1423(2) 0.2683(3) 0.0443(9) Uani 1 1 d . . . H14 H 0.3721 0.1002 0.3057 0.053 Uiso 1 1 calc R . . C15 C 0.4194(4) 0.1981(2) 0.2697(3) 0.0511(10) Uani 1 1 d . . . H15 H 0.5144 0.1926 0.3062 0.061 Uiso 1 1 calc R . . C16 C 0.3691(4) 0.2601(2) 0.2203(3) 0.0494(10) Uani 1 1 d . . . H16 H 0.4289 0.2976 0.2250 0.059 Uiso 1 1 calc R . . C17 C -0.0322(3) 0.11767(17) 0.1838(3) 0.0322(8) Uani 1 1 d . . . H17 H -0.0886 0.0744 0.1698 0.039 Uiso 1 1 calc R . . C18 C 0.1434(4) 0.02371(17) 0.2301(3) 0.0340(8) Uani 1 1 d . . . H18A H 0.2270 0.0154 0.2180 0.041 Uiso 1 1 calc R . . H18B H 0.0713 -0.0056 0.1773 0.041 Uiso 1 1 calc R . . C19 C 0.3863(4) 0.0014(2) 0.6231(3) 0.0526(10) Uani 1 1 d . . . H19A H 0.4638 0.0234 0.6149 0.079 Uiso 1 1 calc R . . H19B H 0.4126 -0.0447 0.6566 0.079 Uiso 1 1 calc R . . H19C H 0.3567 0.0307 0.6696 0.079 Uiso 1 1 calc R . . C20 C 0.2729(4) -0.00640(18) 0.5130(3) 0.0361(8) Uani 1 1 d . . . C21 C 0.1459(4) -0.03541(19) 0.4880(3) 0.0399(9) Uani 1 1 d . . . H21 H 0.1127 -0.0551 0.5378 0.048 Uiso 1 1 calc R . . C22 C 0.0782(4) -0.02984(17) 0.3770(3) 0.0352(8) Uani 1 1 d . . . C23 C -0.0602(4) -0.0523(2) 0.3038(3) 0.0491(10) Uani 1 1 d . . . H23A H -0.0768 -0.0402 0.2282 0.074 Uiso 1 1 calc R . . H23B H -0.1265 -0.0286 0.3251 0.074 Uiso 1 1 calc R . . H23C H -0.0685 -0.1030 0.3098 0.074 Uiso 1 1 calc R . . C24 C -0.0485(4) 0.15632(18) 0.2775(3) 0.0377(8) Uani 1 1 d . . . C25 C 0.0519(4) 0.15570(18) 0.3817(3) 0.0431(9) Uani 1 1 d . . . H25 H 0.1350 0.1327 0.3948 0.052 Uiso 1 1 calc R . . C26 C 0.0329(5) 0.1883(2) 0.4679(3) 0.0550(11) Uani 1 1 d . . . H26 H 0.1032 0.1880 0.5390 0.066 Uiso 1 1 calc R . . C27 C -0.0867(6) 0.2207(2) 0.4501(4) 0.0647(14) Uani 1 1 d . . . H27 H -0.0998 0.2425 0.5091 0.078 Uiso 1 1 calc R . . C28 C -0.1892(5) 0.2221(2) 0.3465(5) 0.0655(13) Uani 1 1 d . . . H28 H -0.2723 0.2449 0.3340 0.079 Uiso 1 1 calc R . . C29 C -0.1691(4) 0.1896(2) 0.2606(4) 0.0536(11) Uani 1 1 d . . . H29 H -0.2392 0.1902 0.1895 0.064 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0466(18) 0.0297(15) 0.0375(16) -0.0011(12) 0.0134(14) -0.0040(13) N2 0.0366(17) 0.0325(15) 0.0335(15) -0.0022(12) 0.0108(13) -0.0038(12) N3 0.0383(16) 0.0255(14) 0.0353(16) 0.0021(11) 0.0103(13) 0.0000(12) N4 0.0328(15) 0.0268(14) 0.0346(15) 0.0022(11) 0.0112(12) 0.0030(12) N5 0.0351(16) 0.0336(16) 0.0375(16) 0.0015(12) 0.0096(13) 0.0026(12) N6 0.0350(16) 0.0296(15) 0.0345(16) 0.0019(12) 0.0116(13) 0.0034(12) C1 0.076(3) 0.043(2) 0.053(2) -0.0033(18) 0.029(2) -0.019(2) C2 0.051(2) 0.039(2) 0.0324(18) -0.0072(15) 0.0169(17) -0.0116(17) C3 0.037(2) 0.054(2) 0.039(2) -0.0038(17) 0.0124(17) -0.0108(17) C4 0.038(2) 0.043(2) 0.0295(17) -0.0041(14) 0.0099(15) 0.0008(16) C5 0.048(2) 0.052(2) 0.049(2) 0.0043(19) 0.0137(19) 0.0075(19) C6 0.0369(19) 0.0326(18) 0.0330(18) -0.0011(14) 0.0122(15) -0.0058(15) C7 0.0391(19) 0.0266(17) 0.0324(17) 0.0006(13) 0.0124(15) -0.0032(14) C8 0.050(2) 0.0326(19) 0.045(2) 0.0051(16) 0.0140(18) 0.0015(16) C9 0.070(3) 0.0273(19) 0.045(2) 0.0062(16) 0.017(2) -0.0010(18) C10 0.066(3) 0.033(2) 0.042(2) -0.0005(16) 0.023(2) -0.0125(18) C11 0.051(2) 0.036(2) 0.0359(19) -0.0014(15) 0.0187(17) -0.0118(16) C12 0.041(2) 0.0295(17) 0.0292(17) -0.0039(13) 0.0156(15) -0.0065(14) C13 0.0337(18) 0.0362(18) 0.0284(17) 0.0006(14) 0.0119(14) -0.0044(14) C14 0.040(2) 0.048(2) 0.042(2) 0.0067(17) 0.0145(17) -0.0020(17) C15 0.033(2) 0.066(3) 0.049(2) 0.004(2) 0.0118(17) -0.0091(19) C16 0.047(2) 0.054(2) 0.047(2) -0.0007(18) 0.0179(19) -0.0192(19) C17 0.0335(18) 0.0266(16) 0.0354(18) 0.0016(13) 0.0126(15) -0.0017(14) C18 0.043(2) 0.0258(17) 0.0317(18) 0.0016(13) 0.0134(15) 0.0047(14) C19 0.052(2) 0.057(3) 0.040(2) 0.0050(18) 0.0091(19) 0.006(2) C20 0.040(2) 0.0324(18) 0.0314(18) 0.0036(14) 0.0096(15) 0.0062(15) C21 0.047(2) 0.0363(19) 0.038(2) 0.0037(15) 0.0185(17) 0.0061(16) C22 0.040(2) 0.0260(17) 0.042(2) 0.0029(14) 0.0183(16) 0.0007(14) C23 0.048(2) 0.050(2) 0.048(2) 0.0065(18) 0.0175(19) -0.0059(18) C24 0.044(2) 0.0301(18) 0.046(2) -0.0013(15) 0.0258(18) -0.0048(15) C25 0.062(2) 0.0289(18) 0.041(2) 0.0031(15) 0.0238(19) -0.0014(17) C26 0.095(3) 0.033(2) 0.047(2) -0.0008(17) 0.038(2) -0.006(2) C27 0.106(4) 0.044(2) 0.073(3) -0.012(2) 0.065(3) -0.016(3) C28 0.062(3) 0.056(3) 0.101(4) -0.012(3) 0.057(3) -0.003(2) C29 0.048(2) 0.050(2) 0.068(3) -0.011(2) 0.028(2) -0.0053(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.336(5) . ? N1 N2 1.367(4) . ? N2 C4 1.362(4) . ? N2 C6 1.450(4) . ? N3 C7 1.445(4) . ? N3 C17 1.467(4) . ? N3 C6 1.479(4) . ? N4 C13 1.393(4) . ? N4 C18 1.435(4) . ? N4 C17 1.456(4) . ? N5 C20 1.333(4) . ? N5 N6 1.367(4) . ? N6 C22 1.364(4) . ? N6 C18 1.458(4) . ? C1 C2 1.503(5) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.386(5) . ? C3 C4 1.370(5) . ? C3 H3 0.9500 . ? C4 C5 1.493(5) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.369(5) . ? C7 C12 1.420(5) . ? C8 C9 1.409(5) . ? C8 H8 0.9500 . ? C9 C10 1.359(6) . ? C9 H9 0.9500 . ? C10 C11 1.414(5) . ? C10 H10 0.9500 . ? C11 C16 1.410(6) . ? C11 C12 1.416(5) . ? C12 C13 1.440(5) . ? C13 C14 1.369(5) . ? C14 C15 1.403(5) . ? C14 H14 0.9500 . ? C15 C16 1.361(6) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C24 1.523(5) . ? C17 H17 1.0000 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.499(5) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C21 1.391(5) . ? C21 C22 1.371(5) . ? C21 H21 0.9500 . ? C22 C23 1.486(5) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 C25 1.382(5) . ? C24 C29 1.384(5) . ? C25 C26 1.394(5) . ? C25 H25 0.9500 . ? C26 C27 1.365(7) . ? C26 H26 0.9500 . ? C27 C28 1.386(7) . ? C27 H27 0.9500 . ? C28 C29 1.395(6) . ? C28 H28 0.9500 . ? C29 H29 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 N2 104.1(3) . . ? N1 N2 C4 112.5(3) . . ? N1 N2 C6 119.4(3) . . ? C4 N2 C6 128.0(3) . . ? C7 N3 C17 109.8(3) . . ? C7 N3 C6 110.7(3) . . ? C17 N3 C6 112.1(3) . . ? C13 N4 C18 123.3(3) . . ? C13 N4 C17 116.5(3) . . ? C18 N4 C17 120.1(3) . . ? C20 N5 N6 104.5(3) . . ? C22 N6 N5 111.9(3) . . ? C22 N6 C18 129.1(3) . . ? N5 N6 C18 118.8(3) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 111.3(3) . . ? N1 C2 C1 120.0(4) . . ? C3 C2 C1 128.7(4) . . ? C4 C3 C2 106.9(3) . . ? C4 C3 H3 126.6 . . ? C2 C3 H3 126.6 . . ? N2 C4 C3 105.3(3) . . ? N2 C4 C5 122.4(3) . . ? C3 C4 C5 132.3(3) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N2 C6 N3 110.8(3) . . ? N2 C6 H6A 109.5 . . ? N3 C6 H6A 109.5 . . ? N2 C6 H6B 109.5 . . ? N3 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? C8 C7 C12 120.3(3) . . ? C8 C7 N3 120.5(3) . . ? C12 C7 N3 119.2(3) . . ? C7 C8 C9 120.0(4) . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C10 C9 C8 120.7(4) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C9 C10 C11 121.3(3) . . ? C9 C10 H10 119.4 . . ? C11 C10 H10 119.4 . . ? C10 C11 C16 123.0(3) . . ? C10 C11 C12 118.2(4) . . ? C16 C11 C12 118.8(3) . . ? C7 C12 C13 120.9(3) . . ? C7 C12 C11 119.6(3) . . ? C13 C12 C11 119.5(3) . . ? C14 C13 N4 123.9(3) . . ? C14 C13 C12 119.5(3) . . ? N4 C13 C12 116.6(3) . . ? C13 C14 C15 120.1(4) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C16 C15 C14 121.7(4) . . ? C16 C15 H15 119.1 . . ? C14 C15 H15 119.1 . . ? C15 C16 C11 120.4(3) . . ? C15 C16 H16 119.8 . . ? C11 C16 H16 119.8 . . ? N3 C17 N4 111.0(3) . . ? N3 C17 C24 110.1(3) . . ? N4 C17 C24 113.8(3) . . ? N3 C17 H17 107.2 . . ? N4 C17 H17 107.2 . . ? C24 C17 H17 107.2 . . ? N4 C18 N6 114.7(3) . . ? N4 C18 H18A 108.6 . . ? N6 C18 H18A 108.6 . . ? N4 C18 H18B 108.6 . . ? N6 C18 H18B 108.6 . . ? H18A C18 H18B 107.6 . . ? C20 C19 H19A 109.5 . . ? C20 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C20 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N5 C20 C21 111.5(3) . . ? N5 C20 C19 120.4(3) . . ? C21 C20 C19 128.1(3) . . ? C22 C21 C20 106.2(3) . . ? C22 C21 H21 126.9 . . ? C20 C21 H21 126.9 . . ? N6 C22 C21 106.0(3) . . ? N6 C22 C23 123.3(3) . . ? C21 C22 C23 130.7(3) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C25 C24 C29 118.5(4) . . ? C25 C24 C17 121.6(3) . . ? C29 C24 C17 119.9(3) . . ? C24 C25 C26 120.9(4) . . ? C24 C25 H25 119.5 . . ? C26 C25 H25 119.5 . . ? C27 C26 C25 120.0(4) . . ? C27 C26 H26 120.0 . . ? C25 C26 H26 120.0 . . ? C26 C27 C28 120.3(4) . . ? C26 C27 H27 119.8 . . ? C28 C27 H27 119.8 . . ? C27 C28 C29 119.3(4) . . ? C27 C28 H28 120.4 . . ? C29 C28 H28 120.4 . . ? C24 C29 C28 121.0(4) . . ? C24 C29 H29 119.5 . . ? C28 C29 H29 119.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.595 _refine_diff_density_min -0.525 _refine_diff_density_rms 0.170 # Attachment 'a9100.cif' data_a9100 _database_code_depnum_ccdc_archive 'CCDC 722447' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C33 H36 Cl Cu N8 O4' _chemical_formula_sum 'C33 H36 Cl Cu N8 O4' _chemical_formula_weight 707.69 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.6294(2) _cell_length_b 17.6905(3) _cell_length_c 17.6917(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.0050(10) _cell_angle_gamma 90.00 _cell_volume 3308.48(10) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.45 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.421 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1472 _exptl_absorpt_coefficient_mu 0.792 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6655 _exptl_absorpt_correction_T_max 0.7171 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23078 _diffrn_reflns_av_R_equivalents 0.0242 _diffrn_reflns_av_sigmaI/netI 0.0223 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 25.02 _reflns_number_total 5821 _reflns_number_gt 5019 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0927P)^2^+4.1248P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment fixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5821 _refine_ls_number_parameters 426 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0569 _refine_ls_R_factor_gt 0.0470 _refine_ls_wR_factor_ref 0.1567 _refine_ls_wR_factor_gt 0.1412 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.092 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4612(4) 0.7712(2) 0.1557(2) 0.0452(9) Uani 1 1 d . . . H1A H 0.4158 0.7666 0.2010 0.068 Uiso 1 1 calc R . . H1B H 0.5506 0.7821 0.1712 0.068 Uiso 1 1 calc R . . H1C H 0.4539 0.7237 0.1271 0.068 Uiso 1 1 calc R . . C2 C 0.4047(3) 0.83437(18) 0.10664(19) 0.0312(7) Uani 1 1 d . . . C3 C 0.4382(3) 0.85981(19) 0.0374(2) 0.0331(7) Uani 1 1 d . . . H3 H 0.5029 0.8398 0.0100 0.040 Uiso 1 1 calc R . . C4 C 0.3601(3) 0.91956(18) 0.01608(18) 0.0287(7) Uani 1 1 d . . . C5 C 0.3518(3) 0.9682(2) -0.05359(18) 0.0322(7) Uani 1 1 d . . . H5A H 0.2849 1.0059 -0.0510 0.048 Uiso 1 1 calc R . . H5B H 0.3323 0.9366 -0.0988 0.048 Uiso 1 1 calc R . . H5C H 0.4329 0.9939 -0.0565 0.048 Uiso 1 1 calc R . . C6 C 0.1737(3) 0.97948(18) 0.07204(17) 0.0256(6) Uani 1 1 d . . . H6A H 0.1799 1.0200 0.0341 0.031 Uiso 1 1 calc R . . H6B H 0.0952 0.9507 0.0573 0.031 Uiso 1 1 calc R . . C7 C 0.2580(3) 1.06362(16) 0.17684(17) 0.0237(6) Uani 1 1 d . . . C8 C 0.3494(3) 1.09547(18) 0.13739(19) 0.0287(7) Uani 1 1 d . . . H8 H 0.3523 1.0835 0.0852 0.034 Uiso 1 1 calc R . . C9 C 0.4385(3) 1.14552(19) 0.1738(2) 0.0339(7) Uani 1 1 d . . . H9 H 0.5010 1.1671 0.1458 0.041 Uiso 1 1 calc R . . C10 C 0.4371(3) 1.16381(19) 0.2486(2) 0.0332(7) Uani 1 1 d . . . H10 H 0.4970 1.1988 0.2719 0.040 Uiso 1 1 calc R . . C11 C 0.3463(3) 1.13072(18) 0.29171(19) 0.0296(7) Uani 1 1 d . . . C12 C 0.2557(3) 1.08034(16) 0.25591(18) 0.0242(6) Uani 1 1 d . . . C13 C 0.1691(3) 1.04323(17) 0.29966(17) 0.0238(6) Uani 1 1 d . . . C14 C 0.1768(3) 1.0544(2) 0.37664(18) 0.0323(7) Uani 1 1 d . . . H14 H 0.1218 1.0279 0.4063 0.039 Uiso 1 1 calc R . . C15 C 0.2665(3) 1.1056(2) 0.4117(2) 0.0391(8) Uani 1 1 d . . . H15 H 0.2706 1.1135 0.4650 0.047 Uiso 1 1 calc R . . C16 C 0.3472(3) 1.1437(2) 0.3707(2) 0.0366(8) Uani 1 1 d . . . H16 H 0.4047 1.1793 0.3953 0.044 Uiso 1 1 calc R . . C17 C 0.0499(3) 1.00977(16) 0.18027(16) 0.0222(6) Uani 1 1 d . . . H17 H -0.0004 0.9661 0.1575 0.027 Uiso 1 1 calc R . . C18 C 0.0015(3) 0.94522(17) 0.29891(18) 0.0265(6) Uani 1 1 d . . . H18A H -0.0618 0.9214 0.2612 0.032 Uiso 1 1 calc R . . H18B H -0.0444 0.9756 0.3342 0.032 Uiso 1 1 calc R . . C19 C -0.0510(4) 0.8800(2) 0.4529(2) 0.0416(9) Uani 1 1 d . . . H19A H -0.1003 0.9197 0.4249 0.062 Uiso 1 1 calc R . . H19B H -0.0177 0.8991 0.5030 0.062 Uiso 1 1 calc R . . H19C H -0.1054 0.8362 0.4591 0.062 Uiso 1 1 calc R . . C20 C 0.0558(3) 0.85704(18) 0.40990(18) 0.0299(7) Uani 1 1 d . . . C21 C 0.1504(3) 0.80481(19) 0.42754(19) 0.0339(7) Uani 1 1 d . . . H21 H 0.1626 0.7746 0.4721 0.041 Uiso 1 1 calc R . . C22 C 0.2241(3) 0.80507(17) 0.36780(19) 0.0299(7) Uani 1 1 d . . . C23 C 0.3400(3) 0.7605(2) 0.3589(2) 0.0410(8) Uani 1 1 d . . . H23A H 0.3718 0.7735 0.3105 0.062 Uiso 1 1 calc R . . H23B H 0.3200 0.7064 0.3595 0.062 Uiso 1 1 calc R . . H23C H 0.4048 0.7721 0.4009 0.062 Uiso 1 1 calc R . . C24 C -0.0314(3) 1.08104(16) 0.16664(18) 0.0245(6) Uani 1 1 d . . . C25 C -0.0397(3) 1.11643(18) 0.0958(2) 0.0313(7) Uani 1 1 d . . . H25 H 0.0101 1.0985 0.0579 0.038 Uiso 1 1 calc R . . C26 C -0.1198(3) 1.1774(2) 0.0802(2) 0.0438(9) Uani 1 1 d . . . H26 H -0.1255 1.2009 0.0317 0.053 Uiso 1 1 calc R . . C27 C -0.1916(3) 1.2042(2) 0.1353(3) 0.0488(10) Uani 1 1 d . . . H27 H -0.2468 1.2459 0.1245 0.059 Uiso 1 1 calc R . . C28 C -0.1829(3) 1.1703(2) 0.2058(3) 0.0463(10) Uani 1 1 d . . . H28 H -0.2314 1.1889 0.2439 0.056 Uiso 1 1 calc R . . C29 C -0.1030(3) 1.10869(19) 0.2211(2) 0.0341(7) Uani 1 1 d . . . H29 H -0.0976 1.0854 0.2697 0.041 Uiso 1 1 calc R . . C30 C 0.2631(4) 0.9306(2) 0.5614(2) 0.0468(9) Uani 1 1 d . . . C31 C 0.3723(4) 0.9222(3) 0.5185(3) 0.0589(11) Uani 1 1 d . . . H31A H 0.3957 0.8687 0.5168 0.088 Uiso 1 1 calc R . . H31B H 0.4435 0.9512 0.5432 0.088 Uiso 1 1 calc R . . H31C H 0.3509 0.9409 0.4666 0.088 Uiso 1 1 calc R . . C32 C 0.4078(5) 0.0689(3) 0.6794(3) 0.0657(13) Uani 1 1 d . . . C33 C 0.4052(5) 0.0320(3) 0.7517(3) 0.0726(14) Uani 1 1 d . . . H33A H 0.3631 -0.0172 0.7442 0.109 Uiso 1 1 calc R . . H33B H 0.3587 0.0634 0.7849 0.109 Uiso 1 1 calc R . . H33C H 0.4919 0.0245 0.7752 0.109 Uiso 1 1 calc R . . N1 N 0.3083(3) 0.87586(14) 0.12754(15) 0.0279(6) Uani 1 1 d . . . N2 N 0.2835(2) 0.92856(14) 0.07162(14) 0.0257(5) Uani 1 1 d . . . N3 N 0.1672(2) 1.01262(14) 0.14519(14) 0.0246(5) Uani 1 1 d . . . N4 N 0.0822(2) 0.99356(14) 0.26051(14) 0.0235(5) Uani 1 1 d . . . N5 N 0.0750(2) 0.88640(14) 0.34156(14) 0.0258(6) Uani 1 1 d . . . N6 N 0.1783(2) 0.85413(15) 0.31447(15) 0.0266(6) Uani 1 1 d . . . N7 N 0.1792(4) 0.9388(3) 0.5931(3) 0.0706(12) Uani 1 1 d . . . N8 N 0.4071(7) 0.0980(3) 0.6224(3) 0.107(2) Uani 1 1 d . . . O1 O 0.7951(5) 0.8688(3) 0.1605(3) 0.0751(15) Uiso 0.70 1 d P A 1 O1' O 0.8209(12) 0.8299(8) 0.1801(7) 0.072(3) Uiso 0.30 1 d P A 2 O2 O 0.9866(4) 0.8325(2) 0.1161(3) 0.1073(16) Uani 1 1 d . A . O3 O 0.8231(5) 0.7484(2) 0.1009(3) 0.126(2) Uani 1 1 d . A . O4' O 0.8642(14) 0.8883(8) 0.0584(8) 0.085(4) Uiso 0.30 1 d P A 3 O4 O 0.7960(6) 0.8545(3) 0.0324(3) 0.0796(15) Uiso 0.70 1 d P A 4 Cl1 Cl 0.85224(8) 0.82501(5) 0.10397(5) 0.0382(2) Uani 1 1 d . . . Cu1 Cu 0.23195(3) 0.87236(2) 0.21849(2) 0.02842(16) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.047(2) 0.039(2) 0.051(2) 0.0087(17) 0.0150(18) 0.0163(17) C2 0.0286(16) 0.0282(16) 0.0374(19) -0.0037(14) 0.0061(13) 0.0028(13) C3 0.0280(16) 0.0368(18) 0.0362(19) -0.0057(14) 0.0113(14) 0.0057(13) C4 0.0262(15) 0.0328(17) 0.0280(17) -0.0061(13) 0.0072(12) -0.0037(13) C5 0.0292(16) 0.0397(18) 0.0289(17) -0.0018(14) 0.0095(13) -0.0020(14) C6 0.0241(14) 0.0304(16) 0.0216(15) -0.0025(12) 0.0001(11) 0.0054(12) C7 0.0213(14) 0.0218(14) 0.0274(16) -0.0003(12) 0.0005(12) 0.0048(11) C8 0.0273(15) 0.0301(16) 0.0291(17) 0.0005(13) 0.0051(13) 0.0012(13) C9 0.0266(16) 0.0323(17) 0.043(2) 0.0028(15) 0.0073(14) -0.0039(13) C10 0.0253(15) 0.0313(17) 0.042(2) -0.0053(14) -0.0002(14) -0.0050(13) C11 0.0248(15) 0.0289(17) 0.0341(18) -0.0035(13) -0.0015(13) 0.0030(12) C12 0.0198(13) 0.0237(15) 0.0283(16) -0.0014(12) -0.0007(11) 0.0051(11) C13 0.0232(14) 0.0230(15) 0.0243(15) -0.0015(12) -0.0015(11) 0.0047(11) C14 0.0301(16) 0.0406(19) 0.0262(17) -0.0027(14) 0.0025(13) 0.0003(14) C15 0.0363(18) 0.053(2) 0.0272(18) -0.0114(16) -0.0025(14) 0.0007(16) C16 0.0292(16) 0.0437(19) 0.0355(19) -0.0114(16) -0.0035(14) -0.0027(14) C17 0.0215(13) 0.0230(14) 0.0215(15) -0.0010(11) 0.0004(11) -0.0007(11) C18 0.0257(15) 0.0268(15) 0.0275(16) 0.0007(13) 0.0047(12) 0.0012(12) C19 0.045(2) 0.050(2) 0.033(2) 0.0050(16) 0.0165(16) 0.0026(16) C20 0.0352(17) 0.0298(16) 0.0254(17) -0.0002(13) 0.0068(13) -0.0034(13) C21 0.0442(19) 0.0287(17) 0.0288(18) 0.0059(13) 0.0039(14) -0.0012(14) C22 0.0334(16) 0.0224(15) 0.0332(18) 0.0017(13) 0.0010(13) 0.0002(13) C23 0.0424(19) 0.0344(19) 0.047(2) 0.0089(16) 0.0064(16) 0.0107(15) C24 0.0194(13) 0.0218(14) 0.0311(16) -0.0039(12) -0.0032(12) -0.0025(11) C25 0.0269(15) 0.0277(16) 0.0376(19) 0.0032(14) -0.0050(13) -0.0050(13) C26 0.0361(18) 0.0316(18) 0.060(2) 0.0131(17) -0.0149(17) -0.0034(15) C27 0.0322(18) 0.0274(18) 0.083(3) 0.0036(19) -0.0102(19) 0.0072(15) C28 0.0307(18) 0.038(2) 0.069(3) -0.0135(19) 0.0005(17) 0.0090(15) C29 0.0280(16) 0.0320(17) 0.042(2) -0.0041(15) 0.0001(14) 0.0046(13) C30 0.050(2) 0.045(2) 0.045(2) -0.0077(17) -0.0016(19) 0.0057(18) C31 0.040(2) 0.065(3) 0.072(3) -0.006(2) 0.008(2) 0.001(2) C32 0.076(3) 0.053(3) 0.068(3) -0.010(2) 0.004(3) -0.018(2) C33 0.075(3) 0.067(3) 0.073(3) 0.009(3) -0.006(3) 0.000(3) N1 0.0293(13) 0.0275(14) 0.0275(14) 0.0006(11) 0.0058(11) 0.0049(10) N2 0.0264(13) 0.0271(13) 0.0240(13) -0.0021(10) 0.0048(10) 0.0019(10) N3 0.0229(12) 0.0283(13) 0.0226(13) -0.0047(10) 0.0025(10) 0.0017(10) N4 0.0237(12) 0.0245(12) 0.0219(13) 0.0001(10) 0.0005(10) -0.0017(10) N5 0.0270(13) 0.0264(13) 0.0247(14) 0.0018(10) 0.0065(10) 0.0025(10) N6 0.0273(13) 0.0247(13) 0.0283(14) 0.0018(11) 0.0062(11) 0.0036(10) N7 0.071(3) 0.075(3) 0.068(3) -0.022(2) 0.021(2) 0.003(2) N8 0.159(6) 0.076(3) 0.084(4) -0.001(3) 0.007(4) -0.043(4) O2 0.062(2) 0.077(3) 0.185(5) -0.037(3) 0.018(3) -0.011(2) O3 0.150(4) 0.052(2) 0.162(5) 0.000(3) -0.050(4) -0.031(3) Cl1 0.0469(5) 0.0302(4) 0.0371(5) -0.0004(3) 0.0020(4) -0.0042(3) Cu1 0.0305(2) 0.0291(2) 0.0268(3) 0.00276(15) 0.00874(17) 0.00599(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.501(5) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 N1 1.343(4) . ? C2 C3 1.386(5) . ? C3 C4 1.373(5) . ? C3 H3 0.9500 . ? C4 N2 1.349(4) . ? C4 C5 1.498(5) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 N3 1.429(4) . ? C6 N2 1.475(4) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.375(4) . ? C7 N3 1.395(4) . ? C7 C12 1.433(4) . ? C8 C9 1.403(5) . ? C8 H8 0.9500 . ? C9 C10 1.364(5) . ? C9 H9 0.9500 . ? C10 C11 1.417(5) . ? C10 H10 0.9500 . ? C11 C12 1.413(4) . ? C11 C16 1.416(5) . ? C12 C13 1.423(4) . ? C13 C14 1.370(4) . ? C13 N4 1.404(4) . ? C14 C15 1.410(5) . ? C14 H14 0.9500 . ? C15 C16 1.359(5) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 N3 1.450(4) . ? C17 N4 1.454(4) . ? C17 C24 1.533(4) . ? C17 H17 1.0000 . ? C18 N4 1.432(4) . ? C18 N5 1.462(4) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.488(5) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 N5 1.351(4) . ? C20 C21 1.377(5) . ? C21 C22 1.379(5) . ? C21 H21 0.9500 . ? C22 N6 1.336(4) . ? C22 C23 1.486(5) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 C29 1.378(5) . ? C24 C25 1.396(5) . ? C25 C26 1.385(5) . ? C25 H25 0.9500 . ? C26 C27 1.382(6) . ? C26 H26 0.9500 . ? C27 C28 1.380(6) . ? C27 H27 0.9500 . ? C28 C29 1.390(5) . ? C28 H28 0.9500 . ? C29 H29 0.9500 . ? C30 N7 1.112(5) . ? C30 C31 1.459(6) . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 N8 1.132(7) . ? C32 C33 1.439(7) . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? N1 N2 1.365(4) . ? N1 Cu1 1.878(3) . ? N5 N6 1.368(4) . ? N6 Cu1 1.875(3) . ? O1 Cl1 1.448(6) . ? O1' Cl1 1.423(13) . ? O2 Cl1 1.428(4) . ? O3 Cl1 1.390(4) . ? O4' Cl1 1.393(14) . ? O4 Cl1 1.440(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 109.9(3) . . ? N1 C2 C1 121.2(3) . . ? C3 C2 C1 128.9(3) . . ? C4 C3 C2 106.8(3) . . ? C4 C3 H3 126.6 . . ? C2 C3 H3 126.6 . . ? N2 C4 C3 106.5(3) . . ? N2 C4 C5 122.9(3) . . ? C3 C4 C5 130.6(3) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N3 C6 N2 111.6(2) . . ? N3 C6 H6A 109.3 . . ? N2 C6 H6A 109.3 . . ? N3 C6 H6B 109.3 . . ? N2 C6 H6B 109.3 . . ? H6A C6 H6B 108.0 . . ? C8 C7 N3 123.9(3) . . ? C8 C7 C12 119.8(3) . . ? N3 C7 C12 116.3(3) . . ? C7 C8 C9 120.3(3) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C10 C9 C8 121.4(3) . . ? C10 C9 H9 119.3 . . ? C8 C9 H9 119.3 . . ? C9 C10 C11 120.1(3) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C12 C11 C16 118.6(3) . . ? C12 C11 C10 119.4(3) . . ? C16 C11 C10 121.9(3) . . ? C11 C12 C13 119.8(3) . . ? C11 C12 C7 119.2(3) . . ? C13 C12 C7 120.9(3) . . ? C14 C13 N4 123.3(3) . . ? C14 C13 C12 120.0(3) . . ? N4 C13 C12 116.7(3) . . ? C13 C14 C15 119.8(3) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C16 C15 C14 121.3(3) . . ? C16 C15 H15 119.3 . . ? C14 C15 H15 119.3 . . ? C15 C16 C11 120.4(3) . . ? C15 C16 H16 119.8 . . ? C11 C16 H16 119.8 . . ? N3 C17 N4 107.4(2) . . ? N3 C17 C24 113.6(2) . . ? N4 C17 C24 112.8(2) . . ? N3 C17 H17 107.6 . . ? N4 C17 H17 107.6 . . ? C24 C17 H17 107.6 . . ? N4 C18 N5 110.8(2) . . ? N4 C18 H18A 109.5 . . ? N5 C18 H18A 109.5 . . ? N4 C18 H18B 109.5 . . ? N5 C18 H18B 109.5 . . ? H18A C18 H18B 108.1 . . ? C20 C19 H19A 109.5 . . ? C20 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C20 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N5 C20 C21 106.6(3) . . ? N5 C20 C19 123.2(3) . . ? C21 C20 C19 130.2(3) . . ? C20 C21 C22 106.5(3) . . ? C20 C21 H21 126.8 . . ? C22 C21 H21 126.8 . . ? N6 C22 C21 110.4(3) . . ? N6 C22 C23 121.0(3) . . ? C21 C22 C23 128.5(3) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C29 C24 C25 118.7(3) . . ? C29 C24 C17 121.7(3) . . ? C25 C24 C17 119.4(3) . . ? C26 C25 C24 120.5(3) . . ? C26 C25 H25 119.7 . . ? C24 C25 H25 119.7 . . ? C27 C26 C25 120.0(4) . . ? C27 C26 H26 120.0 . . ? C25 C26 H26 120.0 . . ? C28 C27 C26 119.9(3) . . ? C28 C27 H27 120.1 . . ? C26 C27 H27 120.1 . . ? C27 C28 C29 119.9(4) . . ? C27 C28 H28 120.1 . . ? C29 C28 H28 120.1 . . ? C24 C29 C28 120.9(4) . . ? C24 C29 H29 119.5 . . ? C28 C29 H29 119.5 . . ? N7 C30 C31 178.2(5) . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? N8 C32 C33 178.5(7) . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C2 N1 N2 105.6(3) . . ? C2 N1 Cu1 128.9(2) . . ? N2 N1 Cu1 125.15(19) . . ? C4 N2 N1 111.2(3) . . ? C4 N2 C6 127.9(3) . . ? N1 N2 C6 120.4(2) . . ? C7 N3 C6 122.1(2) . . ? C7 N3 C17 116.1(2) . . ? C6 N3 C17 119.9(2) . . ? C13 N4 C18 122.4(2) . . ? C13 N4 C17 115.7(2) . . ? C18 N4 C17 119.3(2) . . ? C20 N5 N6 110.8(3) . . ? C20 N5 C18 127.8(3) . . ? N6 N5 C18 121.4(2) . . ? C22 N6 N5 105.7(2) . . ? C22 N6 Cu1 129.0(2) . . ? N5 N6 Cu1 125.2(2) . . ? O3 Cl1 O4' 142.6(7) . . ? O3 Cl1 O1' 91.3(6) . . ? O4' Cl1 O1' 122.9(8) . . ? O3 Cl1 O2 108.1(3) . . ? O4' Cl1 O2 82.1(7) . . ? O1' Cl1 O2 100.4(6) . . ? O3 Cl1 O4 104.4(3) . . ? O4' Cl1 O4 41.8(6) . . ? O1' Cl1 O4 133.9(6) . . ? O2 Cl1 O4 114.6(3) . . ? O3 Cl1 O1 116.2(4) . . ? O4' Cl1 O1 92.3(6) . . ? O1' Cl1 O1 32.6(5) . . ? O2 Cl1 O1 109.3(3) . . ? O4 Cl1 O1 104.4(3) . . ? N6 Cu1 N1 168.98(11) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.886 _refine_diff_density_min -0.696 _refine_diff_density_rms 0.142 # Attachment 'a8978.cif' data_a8978 _database_code_depnum_ccdc_archive 'CCDC 722448' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H32 Cl2 Cu I N6' _chemical_formula_sum 'C30 H32 Cl2 Cu I N6' _chemical_formula_weight 737.96 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.2775(5) _cell_length_b 15.5804(6) _cell_length_c 14.6968(6) _cell_angle_alpha 90.00 _cell_angle_beta 99.0690(10) _cell_angle_gamma 90.00 _cell_volume 3002.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.633 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1480 _exptl_absorpt_coefficient_mu 1.965 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5463 _exptl_absorpt_correction_T_max 0.9081 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21778 _diffrn_reflns_av_R_equivalents 0.0391 _diffrn_reflns_av_sigmaI/netI 0.0386 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 25.03 _reflns_number_total 5312 _reflns_number_gt 4131 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1026P)^2^+5.5093P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment fixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5312 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0746 _refine_ls_R_factor_gt 0.0497 _refine_ls_wR_factor_ref 0.1747 _refine_ls_wR_factor_gt 0.1476 _refine_ls_goodness_of_fit_ref 1.114 _refine_ls_restrained_S_all 1.114 _refine_ls_shift/su_max 0.050 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.9556(5) 0.3975(5) 0.3415(5) 0.0465(18) Uani 1 1 d . . . H1A H 0.9997 0.3834 0.3995 0.070 Uiso 1 1 calc R . . H1B H 0.9702 0.4561 0.3230 0.070 Uiso 1 1 calc R . . H1C H 0.9684 0.3571 0.2936 0.070 Uiso 1 1 calc R . . C2 C 0.8457(5) 0.3914(4) 0.3547(4) 0.0360(15) Uani 1 1 d . . . C3 C 0.7589(5) 0.4063(4) 0.2905(4) 0.0383(15) Uani 1 1 d . . . H3 H 0.7566 0.4210 0.2275 0.046 Uiso 1 1 calc R . . C4 C 0.6775(5) 0.3957(4) 0.3355(4) 0.0365(15) Uani 1 1 d . . . C5 C 0.5661(5) 0.4018(6) 0.3011(5) 0.055(2) Uani 1 1 d . . . H5A H 0.5281 0.3907 0.3520 0.083 Uiso 1 1 calc R . . H5B H 0.5470 0.3591 0.2524 0.083 Uiso 1 1 calc R . . H5C H 0.5497 0.4594 0.2764 0.083 Uiso 1 1 calc R . . C6 C 0.6618(5) 0.3523(4) 0.4995(4) 0.0314(14) Uani 1 1 d . . . H6A H 0.5894 0.3695 0.4831 0.038 Uiso 1 1 calc R . . H6B H 0.6643 0.2893 0.5077 0.038 Uiso 1 1 calc R . . C7 C 0.6985(4) 0.4818(4) 0.5968(4) 0.0272(13) Uani 1 1 d . . . C8 C 0.6451(4) 0.5365(4) 0.5325(4) 0.0353(15) Uani 1 1 d . . . H8 H 0.6077 0.5137 0.4773 0.042 Uiso 1 1 calc R . . C9 C 0.6457(5) 0.6252(5) 0.5480(5) 0.0399(16) Uani 1 1 d . . . H9 H 0.6085 0.6620 0.5033 0.048 Uiso 1 1 calc R . . C10 C 0.6992(5) 0.6596(4) 0.6267(5) 0.0427(17) Uani 1 1 d . . . H10 H 0.6982 0.7199 0.6363 0.051 Uiso 1 1 calc R . . C11 C 0.7557(5) 0.6065(4) 0.6938(4) 0.0352(15) Uani 1 1 d . . . C12 C 0.7550(4) 0.5164(4) 0.6794(4) 0.0280(13) Uani 1 1 d . . . C13 C 0.8164(4) 0.4624(4) 0.7441(4) 0.0270(13) Uani 1 1 d . . . C14 C 0.8762(5) 0.4986(5) 0.8207(5) 0.0388(16) Uani 1 1 d . . . H14 H 0.9180 0.4632 0.8638 0.047 Uiso 1 1 calc R . . C15 C 0.8745(5) 0.5883(5) 0.8342(5) 0.0432(17) Uani 1 1 d . . . H15 H 0.9154 0.6126 0.8867 0.052 Uiso 1 1 calc R . . C16 C 0.8161(6) 0.6401(5) 0.7742(5) 0.0444(17) Uani 1 1 d . . . H16 H 0.8153 0.7000 0.7860 0.053 Uiso 1 1 calc R . . C17 C 0.7225(4) 0.3426(4) 0.6692(4) 0.0253(12) Uani 1 1 d . . . H17 H 0.7349 0.2817 0.6527 0.030 Uiso 1 1 calc R . . C18 C 0.8928(4) 0.3171(4) 0.7680(4) 0.0294(13) Uani 1 1 d . . . H18A H 0.8757 0.2578 0.7468 0.035 Uiso 1 1 calc R . . H18B H 0.8959 0.3187 0.8357 0.035 Uiso 1 1 calc R . . C19 C 1.0929(6) 0.3517(5) 0.9052(5) 0.054(2) Uani 1 1 d . . . H19A H 1.0279 0.3355 0.9240 0.080 Uiso 1 1 calc R . . H19B H 1.1149 0.4074 0.9324 0.080 Uiso 1 1 calc R . . H19C H 1.1445 0.3082 0.9266 0.080 Uiso 1 1 calc R . . C20 C 1.0798(4) 0.3581(4) 0.8026(4) 0.0310(14) Uani 1 1 d . . . C21 C 1.1514(4) 0.3794(4) 0.7468(4) 0.0352(14) Uani 1 1 d . . . H21 H 1.2206 0.3949 0.7663 0.042 Uiso 1 1 calc R . . C22 C 1.1012(4) 0.3733(4) 0.6572(4) 0.0333(14) Uani 1 1 d . . . C23 C 1.1439(5) 0.3894(6) 0.5706(5) 0.054(2) Uani 1 1 d . . . H23A H 1.0908 0.3797 0.5173 0.081 Uiso 1 1 calc R . . H23B H 1.2010 0.3502 0.5676 0.081 Uiso 1 1 calc R . . H23C H 1.1679 0.4488 0.5701 0.081 Uiso 1 1 calc R . . C24 C 0.6306(4) 0.3448(4) 0.7213(4) 0.0272(13) Uani 1 1 d . . . C25 C 0.5340(5) 0.3538(7) 0.6748(5) 0.072(3) Uani 1 1 d . . . H25 H 0.5237 0.3604 0.6097 0.086 Uiso 1 1 calc R . . C26 C 0.4514(6) 0.3535(8) 0.7202(6) 0.087(4) Uani 1 1 d . . . H26 H 0.3850 0.3603 0.6861 0.104 Uiso 1 1 calc R . . C27 C 0.4628(5) 0.3437(4) 0.8129(5) 0.0456(18) Uani 1 1 d . . . H27 H 0.4053 0.3429 0.8440 0.055 Uiso 1 1 calc R . . C28 C 0.5608(6) 0.3350(5) 0.8610(5) 0.053(2) Uani 1 1 d . . . H28 H 0.5710 0.3293 0.9262 0.063 Uiso 1 1 calc R . . C29 C 0.6437(5) 0.3346(5) 0.8150(5) 0.0438(18) Uani 1 1 d . . . H29 H 0.7103 0.3272 0.8486 0.053 Uiso 1 1 calc R . . C30 C 0.6369(9) 0.9524(13) 0.4187(9) 0.156(8) Uani 1 1 d . . . H30A H 0.5830 0.9807 0.3747 0.187 Uiso 1 1 calc R . . H30B H 0.7043 0.9617 0.3994 0.187 Uiso 1 1 calc R . . Cl1 Cl 0.6106(8) 0.8399(5) 0.4340(6) 0.233(3) Uani 1 1 d . . . Cl2 Cl 0.6352(7) 0.9864(5) 0.5381(8) 0.310(5) Uani 1 1 d . . . Cu1 Cu 0.89988(6) 0.32807(5) 0.54957(5) 0.0346(2) Uani 1 1 d . . . I1 I 0.84963(3) 0.15891(3) 0.54610(3) 0.03572(18) Uani 1 1 d . . . N1 N 0.8204(4) 0.3725(3) 0.4361(3) 0.0286(11) Uani 1 1 d . . . N2 N 0.7177(4) 0.3763(3) 0.4240(3) 0.0301(11) Uani 1 1 d . . . N3 N 0.7051(3) 0.3931(3) 0.5842(3) 0.0267(11) Uani 1 1 d . . . N4 N 0.8145(3) 0.3752(3) 0.7253(3) 0.0267(10) Uani 1 1 d . . . N5 N 0.9922(4) 0.3409(3) 0.7448(3) 0.0283(11) Uani 1 1 d . . . N6 N 1.0043(4) 0.3505(3) 0.6551(3) 0.0282(11) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.047(4) 0.053(5) 0.044(4) 0.007(3) 0.023(3) 0.007(3) C2 0.042(4) 0.037(4) 0.032(3) 0.000(3) 0.015(3) 0.003(3) C3 0.046(4) 0.043(4) 0.026(3) 0.004(3) 0.005(3) 0.004(3) C4 0.046(4) 0.042(4) 0.020(3) 0.001(3) 0.002(3) -0.001(3) C5 0.045(4) 0.080(6) 0.034(4) 0.014(4) -0.011(3) 0.006(4) C6 0.027(3) 0.045(4) 0.022(3) 0.000(3) 0.005(2) -0.002(3) C7 0.021(3) 0.036(4) 0.026(3) 0.004(2) 0.011(2) 0.001(2) C8 0.024(3) 0.049(4) 0.032(3) 0.006(3) 0.001(2) 0.002(3) C9 0.030(3) 0.043(4) 0.049(4) 0.013(3) 0.011(3) 0.010(3) C10 0.038(4) 0.035(4) 0.059(5) 0.009(3) 0.020(3) 0.007(3) C11 0.029(3) 0.038(4) 0.043(4) -0.001(3) 0.015(3) 0.000(3) C12 0.022(3) 0.033(3) 0.032(3) -0.002(3) 0.011(2) -0.002(2) C13 0.017(3) 0.038(4) 0.027(3) -0.002(3) 0.008(2) -0.006(2) C14 0.028(3) 0.051(5) 0.037(3) -0.005(3) 0.004(3) -0.004(3) C15 0.037(4) 0.052(5) 0.042(4) -0.015(3) 0.009(3) -0.014(3) C16 0.052(4) 0.037(4) 0.045(4) -0.011(3) 0.012(3) -0.009(3) C17 0.022(3) 0.034(3) 0.020(3) 0.002(2) 0.004(2) -0.002(2) C18 0.019(3) 0.042(4) 0.028(3) 0.007(3) 0.006(2) 0.001(3) C19 0.033(4) 0.084(6) 0.040(4) 0.003(4) -0.008(3) -0.003(4) C20 0.019(3) 0.039(4) 0.034(3) -0.001(3) -0.001(2) 0.003(2) C21 0.020(3) 0.040(4) 0.045(4) -0.003(3) 0.005(3) -0.001(3) C22 0.027(3) 0.035(4) 0.040(3) -0.001(3) 0.011(3) -0.004(3) C23 0.041(4) 0.079(6) 0.047(4) -0.008(4) 0.023(3) -0.018(4) C24 0.020(3) 0.033(4) 0.028(3) 0.001(2) 0.003(2) -0.006(2) C25 0.025(4) 0.161(10) 0.030(4) 0.009(5) 0.002(3) 0.004(5) C26 0.021(4) 0.196(12) 0.043(5) 0.007(6) 0.007(3) -0.002(5) C27 0.034(4) 0.054(5) 0.054(4) 0.002(3) 0.024(3) -0.007(3) C28 0.044(4) 0.080(6) 0.038(4) 0.019(4) 0.015(3) 0.008(4) C29 0.027(3) 0.074(5) 0.032(3) 0.015(3) 0.009(3) 0.012(3) C30 0.070(7) 0.31(2) 0.090(9) -0.084(13) 0.007(6) 0.054(11) Cl1 0.274(9) 0.200(7) 0.220(8) 0.007(5) 0.028(6) 0.025(5) Cl2 0.271(9) 0.232(8) 0.400(14) 0.075(8) -0.030(9) -0.065(7) Cu1 0.0251(4) 0.0547(6) 0.0245(4) 0.0010(3) 0.0052(3) 0.0002(3) I1 0.0399(3) 0.0389(3) 0.0282(3) -0.00194(17) 0.00501(18) 0.00156(18) N1 0.028(3) 0.031(3) 0.027(2) -0.001(2) 0.006(2) -0.001(2) N2 0.029(3) 0.042(3) 0.020(2) 0.002(2) 0.003(2) 0.000(2) N3 0.025(2) 0.033(3) 0.022(2) 0.002(2) 0.0038(19) 0.000(2) N4 0.018(2) 0.032(3) 0.028(2) -0.002(2) 0.0004(19) -0.001(2) N5 0.020(2) 0.039(3) 0.025(2) 0.004(2) 0.0010(19) 0.001(2) N6 0.024(2) 0.035(3) 0.027(2) 0.002(2) 0.007(2) 0.000(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.505(9) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 N1 1.326(8) . ? C2 C3 1.389(9) . ? C3 C4 1.362(9) . ? C3 H3 0.9500 . ? C4 N2 1.360(7) . ? C4 C5 1.489(9) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 N3 1.435(7) . ? C6 N2 1.477(7) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.382(8) . ? C7 N3 1.399(8) . ? C7 C12 1.428(8) . ? C8 C9 1.401(10) . ? C8 H8 0.9500 . ? C9 C10 1.367(10) . ? C9 H9 0.9500 . ? C10 C11 1.409(10) . ? C10 H10 0.9500 . ? C11 C16 1.419(10) . ? C11 C12 1.419(9) . ? C12 C13 1.426(8) . ? C13 C14 1.391(8) . ? C13 N4 1.386(8) . ? C14 C15 1.412(10) . ? C14 H14 0.9500 . ? C15 C16 1.347(11) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 N4 1.453(7) . ? C17 N3 1.463(7) . ? C17 C24 1.540(8) . ? C17 H17 1.0000 . ? C18 N4 1.445(7) . ? C18 N5 1.462(7) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.493(10) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 N5 1.356(7) . ? C20 C21 1.390(9) . ? C21 C22 1.382(9) . ? C21 H21 0.9500 . ? C22 N6 1.331(8) . ? C22 C23 1.494(9) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 C25 1.362(9) . ? C24 C29 1.370(9) . ? C25 C26 1.370(11) . ? C25 H25 0.9500 . ? C26 C27 1.355(12) . ? C26 H26 0.9500 . ? C27 C28 1.387(11) . ? C27 H27 0.9500 . ? C28 C29 1.378(10) . ? C28 H28 0.9500 . ? C29 H29 0.9500 . ? C30 Cl1 1.81(2) . ? C30 Cl2 1.837(15) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? Cu1 N6 1.942(5) . ? Cu1 N1 1.955(5) . ? Cu1 I1 2.7172(9) . ? N1 N2 1.349(7) . ? N5 N6 1.361(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 110.4(6) . . ? N1 C2 C1 121.2(6) . . ? C3 C2 C1 128.3(6) . . ? C4 C3 C2 106.7(5) . . ? C4 C3 H3 126.6 . . ? C2 C3 H3 126.6 . . ? N2 C4 C3 105.6(5) . . ? N2 C4 C5 123.9(6) . . ? C3 C4 C5 130.5(6) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N3 C6 N2 111.1(5) . . ? N3 C6 H6A 109.4 . . ? N2 C6 H6A 109.4 . . ? N3 C6 H6B 109.4 . . ? N2 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? C8 C7 N3 123.7(5) . . ? C8 C7 C12 119.5(6) . . ? N3 C7 C12 116.7(5) . . ? C7 C8 C9 120.5(6) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C10 C9 C8 120.9(6) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C9 C10 C11 120.6(6) . . ? C9 C10 H10 119.7 . . ? C11 C10 H10 119.7 . . ? C10 C11 C16 122.3(6) . . ? C10 C11 C12 119.1(6) . . ? C16 C11 C12 118.5(6) . . ? C11 C12 C13 119.6(5) . . ? C11 C12 C7 119.4(6) . . ? C13 C12 C7 120.9(5) . . ? C14 C13 N4 123.3(6) . . ? C14 C13 C12 119.6(6) . . ? N4 C13 C12 117.0(5) . . ? C13 C14 C15 119.7(6) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? C16 C15 C14 121.4(6) . . ? C16 C15 H15 119.3 . . ? C14 C15 H15 119.3 . . ? C15 C16 C11 121.1(7) . . ? C15 C16 H16 119.5 . . ? C11 C16 H16 119.5 . . ? N4 C17 N3 107.6(4) . . ? N4 C17 C24 111.8(4) . . ? N3 C17 C24 112.4(5) . . ? N4 C17 H17 108.3 . . ? N3 C17 H17 108.3 . . ? C24 C17 H17 108.3 . . ? N4 C18 N5 110.8(5) . . ? N4 C18 H18A 109.5 . . ? N5 C18 H18A 109.5 . . ? N4 C18 H18B 109.5 . . ? N5 C18 H18B 109.5 . . ? H18A C18 H18B 108.1 . . ? C20 C19 H19A 109.5 . . ? C20 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C20 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N5 C20 C21 106.0(5) . . ? N5 C20 C19 124.9(6) . . ? C21 C20 C19 129.1(6) . . ? C20 C21 C22 106.0(5) . . ? C20 C21 H21 127.0 . . ? C22 C21 H21 127.0 . . ? N6 C22 C21 111.1(5) . . ? N6 C22 C23 121.4(6) . . ? C21 C22 C23 127.6(6) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C25 C24 C29 118.4(6) . . ? C25 C24 C17 120.7(6) . . ? C29 C24 C17 120.9(5) . . ? C24 C25 C26 121.2(7) . . ? C24 C25 H25 119.4 . . ? C26 C25 H25 119.4 . . ? C27 C26 C25 121.3(7) . . ? C27 C26 H26 119.4 . . ? C25 C26 H26 119.4 . . ? C26 C27 C28 118.1(6) . . ? C26 C27 H27 121.0 . . ? C28 C27 H27 121.0 . . ? C29 C28 C27 120.5(7) . . ? C29 C28 H28 119.7 . . ? C27 C28 H28 119.7 . . ? C24 C29 C28 120.5(6) . . ? C24 C29 H29 119.7 . . ? C28 C29 H29 119.7 . . ? Cl1 C30 Cl2 97.5(10) . . ? Cl1 C30 H30A 112.3 . . ? Cl2 C30 H30A 112.3 . . ? Cl1 C30 H30B 112.3 . . ? Cl2 C30 H30B 112.3 . . ? H30A C30 H30B 109.9 . . ? N6 Cu1 N1 147.0(2) . . ? N6 Cu1 I1 109.37(15) . . ? N1 Cu1 I1 103.29(15) . . ? C2 N1 N2 105.4(5) . . ? C2 N1 Cu1 132.0(4) . . ? N2 N1 Cu1 121.8(4) . . ? N1 N2 C4 111.8(5) . . ? N1 N2 C6 120.5(4) . . ? C4 N2 C6 127.4(5) . . ? C7 N3 C6 121.8(5) . . ? C7 N3 C17 115.0(4) . . ? C6 N3 C17 119.3(5) . . ? C13 N4 C18 122.5(5) . . ? C13 N4 C17 116.3(5) . . ? C18 N4 C17 120.7(5) . . ? C20 N5 N6 111.4(5) . . ? C20 N5 C18 128.4(5) . . ? N6 N5 C18 120.2(5) . . ? C22 N6 N5 105.5(5) . . ? C22 N6 Cu1 129.2(4) . . ? N5 N6 Cu1 125.1(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 2.069 _refine_diff_density_min -1.115 _refine_diff_density_rms 0.327